Nowadays, Wolf’s posts generate pages of comments denouncing him as a fascist and the toady of an authoritarian president — or lionizing him as a loyal Trump soldier. His aggressive use of federal force to counter protests in Portland, Ore., during the past several weeks has drawn criticism from former DHS officials in both parties; when protesters picketed Wolf’s Alexandria, Va., home last month, his neighbors served them snacks.
Wolf’s journey from mid-level lobbyist to DHS staffer to the face of the president’s police crackdown on protesters whom Trump calls “anarchists” has taken a roundabout path that says as much about the trajectory of the DHS under Trump as the person now running the department. The use of the DHS as an instrument of the president’s agenda — first at the Mexican border and now in U.S. cities — has alarmed many who have come to see the department as the enforcement arm of Trump’s “Make America Great Again” plans, and Wolf as his enabler.
After 3½ years, the president finally is happy with a DHS chief, according to White House aides. And while Wolf’s predecessors sometimes pushed back at Trump’s attempts to break rules and bend norms to fit his desired policies, Trump now has a DHS chief giving him the answers he wants.
“The president likes having someone who will tell him yes,” said David Lapan, a former DHS spokesman, retired Marine colonel and longtime aide to Marine Gen. John F. Kelly who worked closely with Wolf.
Trump “wants people who will agree with him and will go out and act aggressively, and that reaffirms why the president sees Chad favorably,” Lapan said. “But that only lasts so long. And there are plenty of others who were seen favorably by the president until they weren’t.”
Wolf’s ascent to the top of the DHS also is a result of the president’s unprecedented disregard for the norms of the nation’s confirmation processes. The department has not had a Senate-confirmed secretary since April 2019, when Trump ousted Kirstjen Nielsen. Her replacement, Kevin McAleenan, was frustrated at the increasing politicization of the DHS and resigned after seven months. When Wolf took over last November, he wasn’t Trump’s first choice for the job, and he was viewed at the time as an option of last resort — more of a caretaker than a Cabinet secretary.
Wolf was serving then as the DHS’s top policy official, and he was content in that job, according to longtime colleagues who, like others, spoke on the condition of anonymity to share candid views of the DHS chief and his relationship with the president.
Trump had appointed Ken Cuccinelli and Mark Morgan to key DHS roles after seeing them defend his immigration agenda on television, but neither man was eligible for the acting secretary job.
So it went to Wolf, 44, who had a reputation as a competent staffer and political operative. But he was not known publicly as an ideologue or a Trump true believer. His résumé lacked law enforcement and military service, and Wolf had never headed a large organization, after spending much of his career as a lobbyist for the travel industry. On TV, he seemed to lack Cuccinelli’s confidence and Morgan’s zeal.
During the past several weeks, amid his standoff with protesters in Portland, Wolf has eclipsed both men to win the president’s favor, wielding the considerable might of the DHS and sending its most highly trained agents to face off against demonstrators targeting a federal courthouse downtown.
As images surfaced last month of camouflaged federal agents grabbing suspects off the streets and stuffing them into unmarked vehicles, Wolf dug in. The president was eager to use the courthouse standoff for his law-and-order campaign theme, and he threatened to send federal forces elsewhere, focusing on liberal cities run by Democrats.
Critics said Wolf’s intervention in Portland marked a new low in the DHS’s transformation from a counterterrorism agency with broad bipartisan support into a partisan tool. Created after the Sept. 11, 2001, terrorist attacks primarily as a bulwark against national security threats, the department’s focus has shifted to the border and immigration enforcement, becoming a primary instrument of the president’s political agenda.
In Portland, many critics saw a new instance of DHS mission creep, as America’s sprawling domestic security apparatus turned inward to intervene in street-level politics.
“DHS is not going to back down from our responsibilities,” Wolf said on “Fox & Friends” at the height of the Portland unrest, when the city’s mayor blamed Trump for making the violence worse. “I think the president’s been very clear. He’s not going to stand for this.”
Trump called Wolf frequently during the Portland standoff, sometimes early in the morning, when action on the streets was still playing out on the West Coast, according to administration officials who were not authorized to discuss the conversations. Wolf declined requests for an interview for this article.
Sarah Matthews, a White House spokeswoman, called Wolf a “a tremendous asset to the department and the president’s mission” who has been “instrumental in helping implement policies responsible for protecting the American people and our homeland.”
One senior White House official said Trump was initially skeptical of Wolf, and after one of Wolf’s first meetings with the president, Trump did not come away impressed. But since then, he has come to view him as an ally and a proponent of his agenda, and Wolf regularly talks to Stephen Miller, a top Trump aide who controls White House immigration policy. Nielsen, Wolf’s former boss at DHS, had an antagonistic relationship with Miller.
Once hesitant, Wolf now looks for opportunities to do conservative media hits, the senior official said. His rhetoric has become more bellicose, in contrast to his predecessors, who avoided inflammatory language. Wolf in recent weeks has even ditched his stylized five-o’clock-shadow beard — junior staffers joked that he looked like a Washington version of pop star Adam Levine — to assume the clean-cut visage of a cop.
“He sees as key to survival amplifying the White House’s message,” one of these officials said.
Miller, in a statement to The Washington Post provided by the White House, called Wolf “a tireless and profoundly effective champion of the president’s pro-worker immigration policies.”
“Chad is faithfully committed to executing the president’s bold vision of an immigration policy that prioritizes the interests of U.S. workers, wage-earners, taxpayers and communities,” said Miller, who has seized upon the Portland clashes to depict Trump’s intervention in soaring terms, as a struggle between “chaos and civilization.”
Trump likes Wolf, another senior White House official said, because Wolf keeps his briefings short and focuses on topics he knows the president cares about. He also typically brings the president a solution instead of just presenting problems or talking about topics that don’t interest him, the official said. Wolf usually answers the president’s questions quickly and directly, which Trump also likes.
“The president knows Chad just gets things done and he doesn’t have to worry about him,” the official said.
Trump sees Wolf as “serious” and focused on law enforcement, which he views as a key message in his reelection bid, the official said. “He also benefits that the border is under control, and every time Chad talks to him, he can say the numbers have gone down, and the wall is going up.” (After falling sharply, border arrests have been trending upward since April.)
As Wolf hews more closely to the president’s rhetoric and displays a willingness to wield the authorities of the DHS, he has brought rare criticism from the former department leaders under whom he served during the George W. Bush administration — Tom Ridge and Michael Chertoff.
Wolf has been irked by their comments, colleagues say, but mostly blames what he considers inaccurate media coverage of the Portland unrest. But their concerns about overreach are shared by other current and former DHS officials worried that the department is suffering long-term reputational damage.
A trusted aide
Wolf grew up in the wealthy Dallas suburb of Plano, won a tennis scholarship and graduated with a history degree from Southern Methodist University. In the pre-Trump era, he fit the mold of a George W. Bush Republican, with moderately conservative views, a preppy style and a view of government shaped by the 9/11 terrorist attacks.
Wolf worked as an intern on Capitol Hill and was a junior staffer in the office of former senator Chuck Hagel (R-Neb.), then joined the Transportation Security Administration soon after its creation in 2002, where he worked with Nielsen. After leaving the Bush administration in 2005, Wolf became a lobbyist at Wexler Walker, specializing in aviation industry issues, and he remained there for 11 years until Trump’s win, when he was recruited to return to the TSA as the agency’s chief of staff.
Trump had placed Kelly in charge of the DHS, and Nielsen, then Kelly’s chief of staff, wanted to groom Wolf to take over for her in the hope she would be picked to lead the department’s new cybersecurity agency, according to former colleagues of both. Wolf left the TSA after four months to become deputy chief of staff at the DHS and the top aide to then-Deputy Secretary Elaine Duke, a career management official who wasn’t comfortable navigating immigration politics. When Kelly and Nielsen left for the White House in the summer of 2017, Wolf moved into the DHS chief of staff role.
Nielsen was confirmed as Kelly’s replacement at the DHS in late 2017, and she relied heavily on Wolf, especially for political advice, colleagues say. Wolf spent a great deal of time in Kelly’s office at the White House trying to help Nielsen save her job and figure out how to please Trump, helping her prepare for meetings and avoid Trump’s explosions, said a former senior official who worked with them. Wolf would often complain about the administration’s haphazard policymaking process and the extraordinary degree of internal fighting in the West Wing.
Current and former aides say Wolf spends less time one-on-one with Trump than some of his predecessors, and he does not clash with Trump or try to correct him.
As Nielsen’s most trusted aide, Wolf played a central role in the “zero tolerance” border crackdown that separated thousands of migrant children from their parents, one of the defining episodes of Trump’s presidency. Like Nielsen, Wolf has displayed little enthusiasm for the politics of immigration enforcement, but unlike her, he has largely avoided blame for the families’ trauma and the policy debacle behind it.
Trump, who treats monthly enforcement numbers from the border as a kind of stock index of DHS performance, had already soured on Nielsen by the time a record wave of Central American families and children had overwhelmed the U.S. immigration system. The president installed McAleenan, the commissioner of U.S. Customs and Border Protection, whose inner circle was made up mostly of former CBP aides and counselors. Wolf was on the outside, but he remained at the DHS as the acting undersecretary for strategy, policy and plans.
Miller, who is viewed at the DHS as a kind of shadow secretary, is well known for going around agency heads to cultivate relationships with their subordinates, and he began calling Wolf more. Miller had clashed at times with McAleenan, who was pushing back against long-delayed plans for an Immigration and Customs Enforcement operation targeting migrant families.
When McAleenan stepped down last fall, he had no clear Senate-confirmed successor at the DHS, and the White House had never bothered to work toward the confirmation of Trump’s other appointees, let alone nominate them.
Though immigration hard-liners were opposed to Wolf, citing his previous lobbying work securing employment visas for overseas tech companies, Miller had a figure already accustomed to his methods and who, unlike Nielsen and McAleenan, would not take offense when he went around him to achieve a desired outcome. “Chad is a guy without a whole lot of ego,” said one former DHS official and longtime colleague. “He’s not a self-promoter, nor a showboat.”
To be eligible for the acting secretary role, Wolf had to be confirmed for his undersecretary job first, and he squeaked by, with a 54-to-41 Senate vote on Nov. 13. Trump made him acting DHS secretary that same day.
Wolf coasted through a rare lull at the DHS in the months after he took over. The responsibility for delivering on Trump’s ambitious border wall construction targets had fallen to Jared Kushner and the Army Corps of Engineers. The border crackdown engineered by McAleenan, relying largely on cooperation with Mexican authorities and a controversial policy making asylum seekers wait outside U.S. territory, had driven migration numbers back down to levels acceptable to the White House.
When the pandemic hit, Cuccinelli, who had a tense relationship with Wolf and was still rumored to be angling for the department’s top job, became the top DHS appointee to the White House coronavirus task force. Wolf was left to run the DHS and implement its new travel and border restrictions.
Then came Portland.
The president in late June issued an executive order pledging to defend U.S. monuments and federal property against “anarchists and left-wing extremists,” placing the DHS on the front lines of a broader cultural reckoning sparked by the killing of George Floyd.
Trump’s reelection chances have been sinking as a result of widespread frustration with his response to the pandemic and the economic crash, but in Portland his campaign saw a place to make a law-and-order pitch, claiming the country would descend into criminal anarchy should former vice president Joe Biden, the presumptive Democratic nominee, win the presidency in November.
Wolf sent teams of agents in tactical gear to Portland ahead of the July Fourth holiday, and the size and intensity of the protests grew as they galvanized around the courthouse and as the building became a symbol of Trump himself. City and state officials accused Wolf of throwing gas onto the flames, particularly after he traveled to Portland and met with sympathetic police union leaders.
Wolf’s colleagues say he believes without reservation that his use of federal agents to protect the courthouse was justified, and he grew more determined after DHS personnel were injured in the clashes. As images circulated more widely of rioters setting fires and launching commercial-grade fireworks at officers, the optics of the standoff began to change. Some civil rights leaders began criticizing the attacks as a distraction from the racial-justice goals of the Black Lives Matter movement, and they worried the chaos was playing into Trump’s hands.
One former DHS official who worked closely with Wolf said he handled Portland well, and he was not surprised that the president had grown fond of him, calling him “an active listener who doesn’t have an insatiable need to have everybody giving him praise.”
“Chad’s on message,” the official said. “He’s not going out and making gaffes or saying ridiculous things, and that’s helpful in this administration.”
A deal between Trump administration officials and the Oregon governor to de-escalate the situation was reached last week, replacing much of the DHS force at the courthouse with state police officers. Wolf has framed the agreement as a capitulation by authorities in Oregon, insisting that the full contingent of DHS personnel will remain on standby in the city until he is satisfied with the response of local authorities.
But the removal of the federal agents from the front lines defused the standoff almost immediately. Recent nights have brought a diminishing crowd and no arrests. The scenes of swirling gas, explosions and mayhem appear to be over, lending further credence to Oregon officials who said Trump and Wolf were stoking conflict.
Trump appeared eager Friday to keep the conflict going, threatening Portland with National Guard troops despite the first night of calm in weeks.
The president has pledged to deploy federal forces to other cities where homicides and other crimes have risen during the past several months, but Wolf’s potential role is unclear. Some Democrats have indicated a willingness to accept the help, even as the president blames them for the violence, but they have stated a preference to work with the FBI, the U.S. Marshals and other agencies under the command of the Justice Department, not the DHS.